Proper footwear fit for business and the fall season

Q What shoes go best with fall and winter clothes? I have a rather conservative office and I like going to high-end restaurants on the weekends. Will my dark leather shoes with white rubber soles be okay for the coming seasons?

A I’m glad you asked and while I don’t want to be harsh I would say they are not appropriate in these environments at any time of the year. First of all, I wouldn’t even name these shoes, I consider them sneakers. I have a hard time accepting the popular look even for a slightly dressier occasion. Sneakers certainly only fit into the most informal office; If you think the rest of your outfit should be chic at a restaurant, think the same about your shoes.

It’s important to tailor clothing for the season and the event, and I firmly believe that shoes often define a man. As long as they’re not gimmicks, most men’s shoes pair well with the attire that brings us into fall. Depending on the occasion and what else you are wearing, some evening shoes are more suitable than others. In the well-dressed world (where sandals and sneakers just won’t do), two types of footwear are acceptable, lace-ups and slip-ons. Both are crafted from smooth, supple leather, and both are at their best when they’re simple, straightforward, and free of unnecessary decorative touches – to ensure they always look appropriate no matter the season or the occasion.

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Leather lace-up shoes worn by well-dressed men are black, dark brown, and sometimes cordovan. Only these colors are suitable for business and evening wear. While other colors such as navy, gray, and tan are perfect for suits and blazers, they are not acceptable for dress shoes. There are essentially three types of lace-up shoes:

• Wingtips – You can wear them all year round, but make sure their level of formality is appropriate (that is, not overly formal) with the other clothing items you wear.

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• Cap-toes – This less elegant style is versatile enough to work with light and casual or dark and dressy suits. They also go perfectly with blazers and jackets or chinos.

• Smooth Toes – These are great shoes to own. A rich dark brown, they are ideal with more relaxed tan and khaki suits; However, in black they are even more elegant than the other two styles and can double as formal shoes with a black tie in a pinch

Every man should also have a few different pairs of slip-on shoes:

• Classic Loafers – Only in the most stuffy traditional circles are these considered unfit for business. They also go with any form of casual wear.

• Boat/deck shoes – These casual slippers offer a much wider range of colors. For example, they can be worn in navy, gray and even bright red.

• Saddle Oxfords – One of the best-dressed guys I know likes to wear flashy two-tone pairs with his casual weekend attire.

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As a bare minimum, I recommend investing in a pair of snazzy, lace-up cap-toe shoes in either dark brown or black and two styles of slip-ons. Remember that simplicity is the key to good taste in all things, and nowhere more so than in shoes.

One last useful note: It’s a smart move to buy a pair of dress shoes before you have to wear them. Even if you don’t wear them often, you’ll be glad you have them when the time comes to wear them. A suit and sneakers (even the contradictory term “dressy sneakers”) just aren’t enough for a job interview, an important meeting, or a wedding. The rush to find a pair of dress shoes before an event limits your options, and wearing brand new shoes that aren’t “broken in” can be so uncomfortable that you don’t enjoy the occasion. Shop on time.

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